Anthraquinone dyestuffs for polyester articles and process for the dyeing thereof



United States Patent ANTHRAQUINONE DYESTUFFS FOR POLYESTER ARTICLES AND PROCESS FOR THE DYEING THEREOF Argento Crotti, Cogliate, Milan, and Pietro Albauese, Milan, Italy, assignors to Aziende Colori Nazionali Aflini ACNA S.p.A., Milan, Italy N 0 Drawing. Filed Mar. 18, 1964, Ser. No. 352,996

Claims priority, application Italy, Mar. 29, 1963, 6,506/ 63 Claims. (Cl. 8-4) Our invention relates to a new class of dyestuffs suitable for the dyeing of polyester materials and to a method for preparing such dyestuffs. The invention also relates to a process for dyeing polyester materials With the aid of the above-mentioned dyestuffs.

We have found, and'this is the basis for the present invention, that compounds of the formula:

Y is OH or N0 Z is N0 or OH;

Y and Z are different from each other and have the effect of dyeing polyester materials of the type characterized as polyethylene terephthalate, such as fibers, films, or manufactured articles, with greenish-blue shades of excellent general fastness properties.

The compounds characterized by the above formula are obtained by condensing at temperatures substantially between 130 and 210 C., preferably between 160 and 210 C., a dinitrodioxyanthraquinone with the selected amine, in high boiling solvents, for instance nitrobenzene, alpha-chloronaphthalene and dichlorobenzene. Upon completion of the reaction, the solvent may be partially removed and/or diluted with ethyl alcohol and the condensation product separated. The molar ratio in the reaction mixture between dinitrodioxyanthraquinone and the amine is between 1:3 and 1:8.

The compounds of Formula 1 dye the polyethylenterephthalate with shades having a very high fastnesses light,

sublimation, wet treatments and dry-cleaning solvents. The following examples will illustrate specific features, without being intended to limit the broader aspects of the invention.

Example 1 The operation is carried out as described in Example I,

.-but 4,8-dinitroantharufine instead of 4,5-dinitrocrysazine is used. A product having a slightly more reddish shade compared with the preceding one, but exhibiting similar fastness characteristics is obtained.

Example 3 0.5 g. of 4,5-dinitrocrysazine, 1.8 g. of 4-aminodiphenylsulphide, and 10 ml. of nitrobenzene are reacted at 180 for 6 hours in the manner set forth in Example 1. The product resulting is identical in characteristics with the material of Example 1.

Example 4 Using the materials of Example 2, but substituting nitrobenzene as the solvent for the alpha-chloronaphthalene yields the dyestuff of Example 2.

We claim:

1. Dyestuffs for polyester fibers having the structure:

0 wherein X is hydrogen, Y and Z are chosen from the 3. A dyestutf according to claim 1, having the structure:

NO: 0 OH I H I 4. The process for the preparation of a dyestuif comprised in the formula:

wherein X is hydrogen, Y and Z are chosen from the group consisting of OH, N0 Y being different from Z, which comprises condensing a dinitrodioxyanthraquinone in a high boiling solvent, at a temperature between 210 C., with an amine'of the type:

wherein X is as set forth above.

5. The process according to claim 4, wherein the condensation is carried out in alpha-chloronaphthalene.

3 4 6. The process according to claim 4, wherein the con- References Cited densation is carried out in nitrobenzene. UNITED STATES PATENTS 7. Dyeing bath characterized by containing at least one dyestufi according to claim 1.

8. Polyester fibers, films, and other manufactured 5 2,845,443 7/1958 Hindermann et a1. 260-380 X 2,859,221 11/1958 Hindermann et a1. 260- 580 X articles dyed in the dye bath according to claim 7. 2,945,867 7/ 1960 Hoefie 6t 0-3 0 9. Polyethylenterephthalate fibers, films and other man- 2,843,448 7/1958 Thummel et ufactured articles dyed in the dye bath according 3,084,015 4/1963 Grossmann et a1 X l i 7, 3,097,909 7/1963 Rhyner et a1 855 X 10. The process of dyeing polyethylenterephthalate 10 3,214,445 10/1965 Hlndermann et a 260-380 3,255,216 6/1966 Hmdermann et a1. 855 X fibers and films, which comprises immersing said fibers and films in aqueous dye baths containing dyestuffs according to claim 1 at temperatures in the range 100- NORMAN G'TORCHINPJ'ImarY Exammer' 150 C. and autogenous pressures. J. T. HERBERT, Assistant Examiner. 

1. DYESTUFFS FOR POLYESTER FIBERS HAVING THE STRUCTURE:
 10. THE PROCESS OF DYEING POLYETHYLENTEREPHTHALATE FIBERS AND FILMS, WHICH COMPRISES IMMERSING SAID FIBERS AND FILMS IN AQUEOUS DYE BATHS CONTAINING DYESTUFFS ACCORDING TO CLAIM 1 AT TEMPERATURES IN THE RANGE 100*150*C. AND AUTOGENOUS PRESSURES. 